Sodium Carbonate → 1-[2-(N-isopropyl-N-heptylamino)propyl]-9-hydroxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

HRID 46530Notes

Reaction equation

HRID 46530 reaction equation
[CH:1]([N:4]([CH:12]([CH3:32])[CH2:13][C:14]1[C:15](=[O:31])[NH:16][CH2:17][CH2:18][CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:29]C)[CH:25]=3)[C:20]=12)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:3])[CH3:2].B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH:1]([N:4]([CH:12]([CH3:32])[CH2:13][C:14]1[C:15](=[O:31])[NH:16][CH2:17][CH2:18][CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([OH:29])[CH:25]=3)[C:20]=12)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 128324391-[2-(N-isopropyl-N-heptylamino)propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Product 1

HCID 128324521-[2-(N-isopropyl-N-heptylamino)propyl]-9-hydroxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The solution of 2.2 g of 1-[2-(N-isopropyl-N-heptylamino)propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, RR racemate in 18 ml of methylene chloride, precooled in a dry ice-acetone bath, is added to 31.3 ml of a similarly cooled 10% solution of boron tribromide in methylene chloride. The mixture is allowed to reach room temperature and is stirred at said temperature overnight. It is cooled in an ice bath, neutralized to pH=9 with 75 ml of saturated aqueous sodium carbonate and stirred at room temperature for 3.5 hours. The methylene chloride layer is separated, washed with water, dried and evaporated. The residue is suspended in diethyl ether, the crystallized material is collected and recrystallized from ethyl acetate to give the 1-[2-(N-isopropyl-N-heptylamino)propyl]-9-hydroxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2one, RR racemate melting at 144°-146°.

Workup

  1. customto reach room temperature
  2. customtemperature overnight
  3. temperatureIt is cooled in an ice bath
  4. stirringstirred at room temperature for 3.5 hours
  5. customThe methylene chloride layer is separated
  6. washwashed with water
  7. customdried
  8. customevaporated
  9. customthe crystallized material is collected
  10. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0de7525bfc8a41fe9e39ad8fb53b3bbf
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

Loading…